TBADT-Mediated Photocatalytic Stereoselective Radical Alkylation of Chiral N-Sulfinyl Imines: Towards Efficient Synthesis of Diverse Chiral Amines

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Chemistry A European J - 2024 - Leone - TBADT‐Mediated Photocatalytic Stereoselective Radical Alkylation of Chiral.pdf (2.51 MB)
Authors
Leone, Matteo
Milton, Joseph P.
Gryko, Dorota ORCID logo 0000-0002-5197-4222
Neuville, Luc
Masson, Géraldine
Date
2024
Journal Title
Journal ISSN
Volume Title
Publisher
Wiley
License
Creative Commons License
Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License
Abstract
Herein we describe a sustainable and efficient photocatalytic method for the stereoselective radical alkylation of chiral sulfinyl imines. By employing readily available non-prefunctionalized radical precursors and the cost-effective TBADT as a direct HAT photocatalyst, we successfully obtain diverse chiral amines with high yields and excellent diastereoselectivity under mild conditions. This method provides an efficient approach for accessing a diverse array of medicinally relevant compounds, including both natural and synthetic α-amino acids, aryl ethyl amines, and other structural motifs commonly found in approved pharmaceuticals and natural product.
Description
Keywords
photocatalysis    HAT    decatungstate    sulfinyl imine    chiral auxiliary    diastereoselectivity
Citation
Chem. Eur. J. 2024, 30, e202400363 (1 of 6). https://doi.org/10.1002/chem.202400363
URI
https://open.icm.edu.pl/handle/123456789/24331
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Artykuły IChO PAN